Cloud env is not loading team plugins (at all) on the first run after plugin repo is modified

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1

Where does the bug appear (feature/product)?

Background Agent (GitHub, Slack, Web, Linear)

Describe the Bug

Entire team plugin is unavailable to cloud agent the first time the agent is run after updating the plugin. Doesn’t recognize skills or rules at all.

Steps to Reproduce

note: our company (enterprise plan) has one internal github repo containing 2 plugins: one required, one defaulted off. Each contains an always rule as well as some Skills.

  • Make an update to a SKILL.md file
  • From the Agents Window, run a cloud agent (without updating the cloud env itself) against a different repo:
    • cat /home/ubuntu/.cursor/plugins/cache/.cloud-plugin-manifest.json
    • Ask it something it can only know if it has read an always rule correctly
    • (same thing for info contained in one of the plugin Skills)
  • In a new cloud agent session (same repo), repeat these same steps.

The results are significantly different (see attached sessions). Perhaps notably, the two .cloud-plugin-manifest.json files contain entirely different createdAt dates. I don’t know exactly when the cloud env was most recently updated, but it could well be the older of the two dates (a few days ago). The newer one (from the second session) appears to be just now, which seems correct.

Having a stale version of the plugin isn’t catastrophic and that seems to only be part of the problem.

The REAL problem is that the agent doesn’t even load the stale version at all. So none of the rules and none of the skills are loaded into the cloud agent session.

I can reproduce this from cursor.com/agents as well as locally using Agents Window.

Expected Behavior

I’d expect to see correct info from the always rule as well as from Skills.

Operating System

MacOS

Version Information

Version: 3.6.31
VS Code Extension API: 1.105.1
Commit: 81fcf2931d7687b4ff3f3017858d0c6dee7e2a60
Date: 2026-05-31T17:46:29.630Z
Layout: glass
Build Type: Stable
Release Track: Default
Electron: 39.8.1
Chromium: 142.0.7444.265
Node.js: 22.22.1
V8: 14.2.231.22-electron.0
xterm.js: 6.1.0-beta.220
OS: Darwin arm64 25.4.0

For AI issues: which model did you use?

Composer 2.5

For AI issues: add Request ID with privacy disabled

First time using the agent after plugin is updated:
bc-bc7d0b75-1951-4310-b604-9285f40f040a

Second time using the agent after plugin is updated:
bc-142e7eb8-16d6-47e2-b474-321dff517f24

Additional Information

The two .cloud-plugin-manifest.json files are clearly different, but I don’t know if that actually matters to Cursor’s internals.

I can run two back-to-back sessions to repro the problem in a couple minutes. If I make an update to the plugin - then wait 15 minutes before doing the back-to-back sessions…I get the same thing. So it doesn’t appear to be a race with updating the plugin’s github repo.

I can repro this from Agents Window as well as from cursor.com/agents

Does this stop you from using Cursor

Sometimes - I can sometimes use Cursor

7

This is a bug affecting cloud agents when a team plugin repo is updated. The first session after an update boots without any plugins because the updated version hasn’t finished being prepared in the background yet. The second session picks them up because the background preparation completes between runs.

Our team has identified the root cause and has a fix in progress. There’s no reliable workaround right now beyond running a second session, which I know isn’t ideal.

We’ll follow up here once the fix ships. Thank you for the detailed report and the request IDs - they’re very helpful.

8

Thanks!